Being a head boy in the very last privileged ‘whites only’ matriculation year (1990) and now, two decades later, finally closing in on my earlier ambitions to become a high school art teacher in democratic South Africa, this work reflects notions of ‘acceptable’ past behavior and history according to those who wrote it – predominantly the victor. Remembering a time in my youth when segregation seemed ‘normal’, I acknowledge the power of institution and education in forming our public perceptions and question to what extent teaching at a private school, an economically privileged institution in South Africa, and by virtue the countries next captains of industry, propagates or alters the hegemony past.